Hydrazine → HCID 54228347, compound

HRID 1384862Notes

Reaction equation

HRID 1384862 reaction equation
[C:1]([O:5][C:6]([C:8]1[C:16]2[CH2:15][CH:14]([CH2:17][N:18]3C(=O)C4C(=CC=CC=4)C3=O)[O:13][CH2:12][C:11]=2[S:10][C:9]=1[NH2:29])=[O:7])([CH3:4])([CH3:3])[CH3:2].NN>C(O)C>[C:1]([O:5][C:6]([C:8]1[C:16]2[CH2:15][CH:14]([CH2:17][NH2:18])[O:13][CH2:12][C:11]=2[S:10][C:9]=1[NH2:29])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 22084100HCID 22084100, compound

Product 1

HCID 54228347HCID 54228347, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-amino-5-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid tert-butyl ester (0.308 g, 0.74 mmol) in absolute ethanol (5 ml) was added hydrazine (47 μl, 1.48 mmol). The reaction was stirred at 80° C. for 4 h and then at room temperature for another 12 h. The precipitate formed was filtered off and the filtrate concentrated in vacuo. To the oily residue was added dichloromethane (15 ml) and the precipitate formed was filtered off. The filtrate was concentrated in vacuo to give 2-amino-5-aminomethyl-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid tert-butyl ester 0.19 g (90%) as a solid.

Workup

  1. waitat room temperature for another 12 h
  2. customThe precipitate formed
  3. filtrationwas filtered off
  4. concentrationthe filtrate concentrated in vacuo
  5. additionTo the oily residue was added dichloromethane (15 ml)
  6. customthe precipitate formed
  7. filtrationwas filtered off
  8. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-388eb201da2a4d2d9b5904536125106c
Source dataset
uspto-grants-2001_07
Patent number
US06262044B1

Reaction notes

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